My first sexual encounter with a mature woman was when I was 16.

The year was 1960. School has just opened up. I was in the 10th grade. I was 6’7”.

The wife of an Army guy had moved in a house on our block. She was 25 and very beautiful. She was a brunette and was about 5’9” tall. As the saying went at the time: she was built. Her son was in the second grade.

School let out at 3pm and she didn’t get home from work till 5:30. She asked my mom if the child could stay with us till she got home? Mom agreed and the deal was sealed at $1.00 per day.

Within a few weeks her husband was deployed on a ship for Europe. Eventually she told my mom that her son was falling behind in school.

Mom told the woman, Ruby, that I had a gift for teaching. So, Ruby asked me if I could tutor her child and that she would pay me when she could.

I agreed. The child’s actual father was not Ruby’s husband. The boy was conceived with another man.

I worked with the boy and it turned out that he was a very quick learner. And the child took to me almost like an older brother. Ruby was very pleased. She informed me that her husband didn’t really like boy and he wouldn’t spend time doing things with the boy.

After some time, Ruby invited me to have dinner with her n the boy. She told me that a dinner would be her way of saying thanks.

The meal went well. After we ate, she turned on her record player. She loved the music of Frank Sinatra. After some time. She called bedtime and I went home.

A few days later, I took the child home. Ruby came home and put on a white cotton gown. She was so alluring. So sexually provocative, that I became aroused. She made some sandwiches for the three of us and invited me to the table. She could see that I was extremely aroused and she did a double take on my crotch. And a slight smile appeared on her lips.

We sat down at the table. The boy was full of excitement about his mom being home. As he talked, Ruby kept glancing at me. She took a slip of paper and wrote a few sentences down on the paper. She finally slipped me the note. It read:

“I’m putting Bobby to bed at 8. Could you come back at 8:30?” I read the note and I read between the lines. I nodded my head in the affirmative.

For the next 2 hours, I was beside myself with anticipation. My only sexual experiences was with girls my own age which involved kissing and mutual Mastrubation.

I returned to her house at the appointed time. She met me wearing her white gown. Her breast jiggled as she opened the door and stepped back. She took my hand and led me to her sofa while she placed her finger to her mouth and reminded me to be very quiet.

She said. “I have something to discuss with you, ok?” I shook my head yes.

She continued. “I think you are a very handsome boy. But you are a boy. If anyone ever found out that I’ve been with you, I would be in a world of trouble. You must never tell anyone. Agreed?”

I shook my head again, and whispered “yes. I understand and I promise.”

Ruby smiled and then opined. “I think that you are a virgin. Am I correct?” She smiled. I was embarrassed. I guess it showed. She stated. Most boys your age are virgins. Are you afraid?”

I told her that I was not afraid and I confessed that I was, indeed, a virgin.

She smiled and said, “I thought so. We should kiss. That usually breaks the ice”.

We kissed and she opened her mouth. She pressed her tongue into my mouth. She reached for my dick, saying “oh my. He’s a big boy like you.” I fondled her breast. She removed her gown. I couldn’t take my eyes off of those beautiful mounds. Her nipples were quite large, Brown in color and about the size of an average cantaloupe. We continued to kiss. Her kisses became more aggressive and urgent. Then she unzipped my wranglers. She removed my hard cock and stroked him several times. She asked me how long he was. I lied and said I didn’t know. She got up. Went to a shelf and returned with a cloth sewing tape measure. She sized him and announced, “As I thought. He’s just a tad over 8” and his girth is 7.5”. That thing is a monster.”

Ruby directed me to remove my jeans and shirt. She retrieved a warm wash cloth and cleaned my crotch area. By then. My dick was raging. She laid back on the sofa. Lifted and removed her gown. I was amazed. She spread her legs and revealed a lush and dark haired pussy. She pulled me and I positioned over her. I felt her hand take my cock. She guided him into her lush pussy. She lifted and began to move. I matched her with a series of counter thrusts. She began to cry. Tears were flowing from her face. I thought that I was hurting her.

At that moment. She kissed me even harder. Sucking on my tongue and responding to my thrusts with her own. My tempo increased. I could feel her pussy becoming even more moist. I felt her hands on my buttocks, encouraging me to go harder and deeper. She lifted again. My cock exploded. I felt spasm after spasm. We continued to kiss.

We continued our relationship for 3 more months. Finally. She moved out of state to be with her military husband.

I never saw her again.

Dear Daddy 3

Written by Son

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